What does a 'caught up' person actually look like?

What does a 'caught up' person look like?

A few years ago, someone asked my wife this question, and it’s haunted both of us ever since. At the time, she'd been frustrated because she was always behind, overwhelmed, underwater. Stop me if this sounds familiar:

We say it like it’s a temporary state. A scheduling issue. Something we can fix with a couple late nights, a new app, and maybe a motivational quote or two.

But the question sticks:

What does a 'caught up' person actually look like?

Because honestly? I have no idea. I don’t think most of us do.

What’s the finish line for adulting? When does the inbox stay empty? When is the house finally clean? When do the habits lock in for good? When do we arrive at the version of ourselves that finally has it all together?

There will always be another email. Another task. Another half-finished thing.

Life never stops never stopping.

And in the last few editions, we've been talking about motivation, systems, the modes of doing... But there's a deeper thing to consider: what if the whole idea of "getting caught up" is fundamentally flawed?

So this week, let's talk about our addiction to moving finish lines, why this mindset is wrecking our productivity, why chasing "caught up" might be fundamentally broken, and how we can find peace with perpetual incompletion.

Our Romance With Moving Targets

More often than not, the moment we achieve something, we immediately recalibrate what "success" looks like.

Cleaned the junk drawer? Cool. Now the closet looks terrible. Inbox got to zero? Great. Now keep it that way. Snazzy new morning routine? Good start. Now make it 5 AM and add meditating.

It's not just perfectionism. It's that uncomfortable mental loop we all run—believing we should be on top of things while reality shows us otherwise. We believe we should be organized. In control. But we're juggling half-done projects, missed calls, and inboxes that multiply like fruit flies. The mind hates this contradiction, so it scrambles to fix it.

We've got a few choices. We can try to change reality (but changing reality is rarely an option), change our self-image (but this could fundamentally threaten who we see ourselves as), or take the more subtle route: shift the definition of what it means to be "on top of things."

For example, I think of myself as someone who cares about being healthy, but the truth is, I haven't worked out in a long time. There's this gap between the version of me I picture and what I'm actually doing. To make that gap feel smaller, I tell myself I've just been too busy. I count the daily dog walks as enough to keep me going. And sure, they help, but I know I'm not really doing what I need. So I do this thing: I shift what "being healthy" actually means. I tell myself, "Once I get my workout area at home set up and figure out my schedule, then I'll get back on track. Then I'll be the healthy person I am."

See what happened there? I didn't change my self-image or accept that I'm not prioritizing health. Instead, I redefined what being "on top of things" looks like. Being healthy went from "working out regularly" to "having a plan to work out regularly." The bar moved, but so subtly I barely noticed. And I bet you've done something similar.

People do this all the time. With our health goals, our inbox management, our morning routines. We chase a different version of the goal, one that makes the present mess feel like just a step along the way. It's a neat psychological trick.

And it's making us miserable because we are always in pursuit. Never arriving.

But there's an even bigger problem with trying to get 'caught up.’

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The Problem With Doing Laundry

Trying to “get caught up” is like trying to finish your laundry—forever.

You can wash, dry, fold, and put away every single item in the house. But unless you plan to go naked tomorrow, you’re already behind again.

Because my friends, laundry isn’t a problem you solve. It’s a process you manage.

Same with email. Same with routines. Same with being a person.

We treat life like a series of finishable tasks, then feel like failures when it doesn’t stay finished.

But life is generative. It creates messes. Every conversation creates follow-ups. Every meal creates dishes. Every success creates new opportunities and responsibilities. Every day we're alive, we generate more inputs than we can process. It's not a bug in the system; it's the feature of being human.

The only way to truly be “done” is to stop engaging with life altogether. Which is a pretty bleak way to think about productivity.

So why do we keep chasing this impossible state? Because we've confused motion with progress, busy with productive, and temporary order with permanent solutions. And when we inevitably fall behind again, instead of questioning the premise, we just redefine success and try again.

Let the Rest Stay Messy

What if, instead of asking "How do I get caught up?" we asked "What deserves my attention right now?"

It sounds simple. But it’s a mindset shift that matters.

When I'm focused on being behind, everything feels urgent. When I focus on what actually matters today, things just fall into place a bit more.

Let me give you a small example. During the early days of the pandemic, our whole family was stuck at home (like most everyone), and the house felt like chaos. So we started doing these 20-minute cleaning bursts.

We’d pair up, pick one part of the house, set a timer, and just do what we could. Then we’d quit.

We weren't trying to clean the whole house. We weren't optimizing our cleaning system. We just picked one area, worked for 20(ish) minutes, then stopped. And it worked. The house got cleaner bit by bit, nobody felt overwhelmed, and we all felt good about what we'd accomplished.

Because we weren’t trying to catch up on everything, we were just deciding what mattered right now. And that was enough.

Maybe it's not about getting everything done. Maybe instead it's about clarity. Knowing what you care about. Knowing what you can let go. And being okay with the fact that there will always be more.

The Bottom Line

So what does a "caught up" person actually look like?

Maybe they don't exist. Maybe the question itself is the problem.

Because here's what I think that person was really asking my wife: What would it feel like to stop running toward a finish line that doesn't exist?

I can't say I know people like this—hell, I'm not even there myself yet. But I have this vision of what it could look like: someone who's made peace with incompletion. They respond to what matters and let the rest wait. They show up for what they can and release what they can't. They've traded the exhausting pursuit of "caught up" for the quieter satisfaction of "enough for today."

They're not behind. They're not ahead. They're just here, in this moment, choosing what deserves their attention.

And maybe that's what a "caught up" person actually does looks like: someone who's stopped chasing the mirage and started living where they are.

The inbox will refill. The laundry will pile up again. Life will keep generating beautiful, messy, endless work.

Cause being caught up was never the goal. Being present was.

As always, thanks for reading,
— Derek
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